Leucocyanidin (BioDeep_00000228427)

Main id: BioDeep_00000005990

 

human metabolite PANOMIX_OTCML-2023 PANOMIX-Anthocyanidin natural product


代谢物信息卡片


2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol

化学式: C15H14O7 (306.0739)
中文名称: 白西尼多, 无色矢车菊素
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: c1(cc(c2c(c1)O[C@H]([C@H]([C@H]2O)O)c1cc(c(cc1)O)O)O)O
InChI: InChI=1S/C15H14O7/c16-7-4-10(19)12-11(5-7)22-15(14(21)13(12)20)6-1-2-8(17)9(18)3-6/h1-5,13-21H

描述信息

Leucocyanidin, also known as 3,3,4,4,5,7-flavanhexol or resivit, is a member of the class of compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-tiol. Thus, leucocyanidin is considered to be a flavonoid lipid molecule. Leucocyanidin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Leucocyanidin can be found in a number of food items such as climbing bean, black mulberry, corn salad, and caraway, which makes leucocyanidin a potential biomarker for the consumption of these food products. Leucocyanidin is a colorless chemical compound that is a member of the class of natural products known as leucoanthocyanidins .
Leucocyanidin is an active anti-ulcerogenic ingredient was extracted from Litchi Chinensis. Leucocyanidin demonstrates a significant protective effect against Aspirin-induced erosions in rat models[1].
Leucocyanidin is an active anti-ulcerogenic ingredient was extracted from Litchi Chinensis. Leucocyanidin demonstrates a significant protective effect against Aspirin-induced erosions in rat models[1].

同义名列表

17 个代谢物同义名

2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol; (+)-2,3-trans-3,4-cis-3,4,5,7,3,4-hexahydroxyflavan; 5,7,3,4-tetrahydroxyflavan-3,4-diol; 3,3,4,4,5,7-hexahydroflavane; 3,3,4,4,5,7-flavanhexanol; 3,3,4,4,5,7-Flavanhexol; Leucoanthocyanidol; Leukocyanidine; flavanhexanol; Leucocyanidin; Leucocianidol; leucodyanidol; Leucocyanidol; 3,4-Cyanidiol; Procyanidol; Venen Tabs; Resivit



数据库引用编号

12 个数据库交叉引用编号

分类词条

相关代谢途径

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代谢反应

0 个相关的代谢反应过程信息。

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BioCyc(0)

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Plant Reactome(0)

INOH(0)

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35 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Peiqiang Wang, Lingjie Zhang, Lei Zhao, Xinfu Zhang, Hanghang Zhang, Yahui Han, Xiaolan Jiang, Yajun Liu, Liping Gao, Tao Xia. Comprehensive Analysis of Metabolic Fluxes from Leucoanthocyanins to Anthocyanins and Proanthocyanidins (PAs). Journal of agricultural and food chemistry. 2020 Dec; 68(51):15142-15153. doi: 10.1021/acs.jafc.0c05048. [PMID: 33307696]
  • Keji Yu, Ji Hyung Jun, Changqing Duan, Richard A Dixon. VvLAR1 and VvLAR2 Are Bifunctional Enzymes for Proanthocyanidin Biosynthesis in Grapevine. Plant physiology. 2019 07; 180(3):1362-1374. doi: 10.1104/pp.19.00447. [PMID: 31092697]
  • Jia-Rong Zhang, Claudine Trossat-Magnin, Katell Bathany, Serge Delrot, Jean Chaudière. Oxidative Transformation of Leucocyanidin by Anthocyanidin Synthase from Vitis vinifera Leads Only to Quercetin. Journal of agricultural and food chemistry. 2019 Apr; 67(13):3595-3604. doi: 10.1021/acs.jafc.8b06968. [PMID: 30865451]
  • Jing Yang, Dawei Qian, Shu Jiang, Er-xin Shang, Jianming Guo, Jin-ao Duan. Identification of rutin deglycosylated metabolites produced by human intestinal bacteria using UPLC-Q-TOF/MS. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2012 Jun; 898(?):95-100. doi: 10.1016/j.jchromb.2012.04.024. [PMID: 22583754]
  • Sabaz Ali Khan, Pierre-Yves Chibon, Ric C H de Vos, Bert A Schipper, Evert Walraven, Jules Beekwilder, Thijs van Dijk, Richard Finkers, Richard G F Visser, Eric W van de Weg, Arnaud Bovy, Alessandro Cestaro, Riccardo Velasco, Evert Jacobsen, Henk J Schouten. Genetic analysis of metabolites in apple fruits indicates an mQTL hotspot for phenolic compounds on linkage group 16. Journal of experimental botany. 2012 May; 63(8):2895-908. doi: 10.1093/jxb/err464. [PMID: 22330898]
  • Yuepeng Han, Sornkanok Vimolmangkang, Ruth Elena Soria-Guerra, Schuyler S Korban. Introduction of apple ANR genes into tobacco inhibits expression of both CHI and DFR genes in flowers, leading to loss of anthocyanin. Journal of experimental botany. 2012 Apr; 63(7):2437-47. doi: 10.1093/jxb/err415. [PMID: 22238451]
  • Li Yuan, Lijun Wang, Zujing Han, Yuanzhong Jiang, Lili Zhao, Hong Liu, Li Yang, Keming Luo. Molecular cloning and characterization of PtrLAR3, a gene encoding leucoanthocyanidin reductase from Populus trichocarpa, and its constitutive expression enhances fungal resistance in transgenic plants. Journal of experimental botany. 2012 Apr; 63(7):2513-24. doi: 10.1093/jxb/err425. [PMID: 22268151]
  • Yung-Fen Huang, Agnès Doligez, Alexandre Fournier-Level, Loïc Le Cunff, Yves Bertrand, Aurélie Canaguier, Cécile Morel, Valérie Miralles, Frédéric Veran, Jean-Marc Souquet, Véronique Cheynier, Nancy Terrier, Patrice This. Dissecting genetic architecture of grape proanthocyanidin composition through quantitative trait locus mapping. BMC plant biology. 2012 Feb; 12(?):30. doi: 10.1186/1471-2229-12-30. [PMID: 22369244]
  • Trupti Joshi, Kapil Patil, Michael R Fitzpatrick, Levi D Franklin, Qiuming Yao, Jeffrey R Cook, Zheng Wang, Marc Libault, Laurent Brechenmacher, Babu Valliyodan, Xiaolei Wu, Jianlin Cheng, Gary Stacey, Henry T Nguyen, Dong Xu. Soybean Knowledge Base (SoyKB): a web resource for soybean translational genomics. BMC genomics. 2012; 13 Suppl 1(?):S15. doi: 10.1186/1471-2164-13-s1-s15. [PMID: 22369646]
  • Jason D Gillman, Ashley Tetlow, Jeong-Deong Lee, J Grover Shannon, Kristin Bilyeu. Loss-of-function mutations affecting a specific Glycine max R2R3 MYB transcription factor result in brown hilum and brown seed coats. BMC plant biology. 2011 Nov; 11(?):155. doi: 10.1186/1471-2229-11-155. [PMID: 22070454]
  • M Horbowicz, W Wiczkowski, Danuta Koczkodaj, M Saniewski. Effects of methyl jasmonate on accumulation of flavonoids in seedlings of common buckwheat (Fagopyrum esculentum Moench). Acta biologica Hungarica. 2011 Sep; 62(3):265-78. doi: 10.1556/abiol.62.2011.3.6. [PMID: 21840829]
  • Sangaalofa T Clark, Wynand S Verwoerd. A systems approach to identifying correlated gene targets for the loss of colour pigmentation in plants. BMC bioinformatics. 2011 Aug; 12(?):343. doi: 10.1186/1471-2105-12-343. [PMID: 21849042]
  • Daneel Ferreira, Christina M Coleman. Towards the synthesis of proanthocyanidins: half a century of innovation. Planta medica. 2011 Jul; 77(11):1071-85. doi: 10.1055/s-0030-1270908. [PMID: 21412691]
  • Lilian Cristina Baldon Aizza, Marcelo Carnier Dornelas. A genomic approach to study anthocyanin synthesis and flower pigmentation in passionflowers. Journal of nucleic acids. 2011; 2011(?):371517. doi: 10.4061/2011/371517. [PMID: 21772993]
  • Ripu M Kunwar, Keshab P Shrestha, Rainer W Bussmann. Traditional herbal medicine in far-west Nepal: a pharmacological appraisal. Journal of ethnobiology and ethnomedicine. 2010 Dec; 6(?):35. doi: 10.1186/1746-4269-6-35. [PMID: 21144003]
  • R Gadekar, P K Singour, P K Chaurasiya, R S Pawar, U K Patil. A potential of some medicinal plants as an antiulcer agents. Pharmacognosy reviews. 2010 Jul; 4(8):136-46. doi: 10.4103/0973-7847.70906. [PMID: 22228953]
  • Yuepeng Han, Sornkanok Vimolmangkang, Ruth Elena Soria-Guerra, Sergio Rosales-Mendoza, Danman Zheng, Anatoli V Lygin, Schuyler S Korban. Ectopic expression of apple F3'H genes contributes to anthocyanin accumulation in the Arabidopsis tt7 mutant grown under nitrogen stress. Plant physiology. 2010 Jun; 153(2):806-20. doi: 10.1104/pp.109.152801. [PMID: 20357139]
  • Bathilde Auger, Cécile Baron, Marie-Odile Lucas, Sonia Vautrin, Hélène Bergès, Boulos Chalhoub, Alain Fautrel, Michel Renard, Nathalie Nesi. Brassica orthologs from BANYULS belong to a small multigene family, which is involved in procyanidin accumulation in the seed. Planta. 2009 Nov; 230(6):1167-83. doi: 10.1007/s00425-009-1017-0. [PMID: 19760260]
  • Feng Xu, Hua Cheng, Rong Cai, Lin Ling Li, Jie Chang, Jun Zhu, Feng Xia Zhang, Liu Ji Chen, Yan Wang, Shu Han Cheng, Shui Yuan Cheng. Molecular cloning and function analysis of an anthocyanidin synthase gene from Ginkgo biloba, and its expression in abiotic stress responses. Molecules and cells. 2008 Dec; 26(6):536-47. doi: . [PMID: 18779661]
  • Jong-Sug Park, Jung-Bong Kim, Kang-Jin Cho, Choong-Ill Cheon, Mi-Kyung Sung, Myoung-Gun Choung, Kyung-Hee Roh. Arabidopsis R2R3-MYB transcription factor AtMYB60 functions as a transcriptional repressor of anthocyanin biosynthesis in lettuce (Lactuca sativa). Plant cell reports. 2008 Jun; 27(6):985-94. doi: 10.1007/s00299-008-0521-1. [PMID: 18317777]
  • Motoki Matsuda, Yuichiro Otsuka, Shigeki Jin, Jun Wasaki, Jun Watanabe, Toshihiro Watanabe, Mitsuru Osaki. Biotransformation of (+)-catechin into taxifolin by a two-step oxidation: primary stage of (+)-catechin metabolism by a novel (+)-catechin-degrading bacteria, Burkholderia sp. KTC-1, isolated from tropical peat. Biochemical and biophysical research communications. 2008 Feb; 366(2):414-9. doi: 10.1016/j.bbrc.2007.11.157. [PMID: 18068670]
  • Yongzhen Pang, Gregory J Peel, Elane Wright, Zengyu Wang, Richard A Dixon. Early steps in proanthocyanidin biosynthesis in the model legume Medicago truncatula. Plant physiology. 2007 Nov; 145(3):601-15. doi: 10.1104/pp.107.107326. [PMID: 17885080]
  • Gordon V Louie, Thomas J Baiga, Marianne E Bowman, Takao Koeduka, John H Taylor, Snejina M Spassova, Eran Pichersky, Joseph P Noel. Structure and reaction mechanism of basil eugenol synthase. PloS one. 2007 Oct; 2(10):e993. doi: 10.1371/journal.pone.0000993. [PMID: 17912370]
  • De-Yu Xie, Lisa A Jackson, John D Cooper, Daneel Ferreira, Nancy L Paiva. Molecular and biochemical analysis of two cDNA clones encoding dihydroflavonol-4-reductase from Medicago truncatula. Plant physiology. 2004 Mar; 134(3):979-94. doi: 10.1104/pp.103.030221. [PMID: 14976232]
  • Sharon Abrahams, Elizabeth Lee, Amanda R Walker, Gregory J Tanner, Philip J Larkin, Anthony R Ashton. The Arabidopsis TDS4 gene encodes leucoanthocyanidin dioxygenase (LDOX) and is essential for proanthocyanidin synthesis and vacuole development. The Plant journal : for cell and molecular biology. 2003 Sep; 35(5):624-36. doi: 10.1046/j.1365-313x.2003.01834.x. [PMID: 12940955]
  • Heather Ray, Min Yu, Patricia Auser, Laureen Blahut-Beatty, Brian McKersie, Steve Bowley, Neil Westcott, Bruce Coulman, Alan Lloyd, Margaret Y Gruber. Expression of anthocyanins and proanthocyanidins after transformation of alfalfa with maize Lc. Plant physiology. 2003 Jul; 132(3):1448-63. doi: 10.1104/pp.103.025361. [PMID: 12857826]
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  • G J Tanner, K N Kristiansen. Synthesis of 3,4-cis-[3H]leucocyanidin and enzymatic reduction to catechin. Analytical biochemistry. 1993 Mar; 209(2):274-7. doi: 10.1006/abio.1993.1119. [PMID: 8470799]
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